Chloroform → HCID 13983511, compound

HRID 1084927Notes

Reaction equation

HRID 1084927 reaction equation
[CH:1]1([CH2:4][S:5]([C:8]2[CH:9]=[C:10]([C:18](O)=[O:19])[C:11]3[O:15][CH:14]([CH3:16])[CH2:13][C:12]=3[CH:17]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.C(Cl)(Cl)Cl.ClC(OCC)=O.[C:31]1([CH2:37][N:38]2[CH2:42][CH2:41][CH2:40][CH:39]2[CH2:43][NH2:44])[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]=1>C(O)(=O)C.O.C(N(CC)CC)C>[C:31]1([CH2:37][N:38]2[CH2:42][CH2:41][CH2:40][CH:39]2[CH2:43][NH:44][C:18]([C:10]2[C:11]3[O:15][CH:14]([CH3:16])[CH2:13][C:12]=3[CH:17]=[C:8]([S:5]([CH2:4][CH:1]3[CH2:3][CH2:2]3)(=[O:7])=[O:6])[CH:9]=2)=[O:19])[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]=1

Participants

8

Reactant 4

HCID 6212ChloroformHCID 10928Ethyl chloroformateHCID 30183171-(1-Cyclohexen-1-ylmethyl)pyrrolidine-2-methylamineHCID 13983510HCID 13983510, compound

Product 1

HCID 13983511HCID 13983511, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

97 g of 5-cyclopropylmethylsulphonyl-2-methyl-2,3-dihydrobenzofuran-7-carboxylic acid, 350 ml of chloroform and 34 g of triethylamine were introduced into a 1-liter round-bottomed flask. The solution was cooled to 0° C. and 36 g of ethyl chloroformate were then added dropwise, while maintaining the temperature between 0° C. and 5° C. The contents were then stirred for 1 hour between 0° C. and 5° C. and 67 g of 1-cyclohexenylmethyl-2-aminomethylpyrrolidine were then poured in dropwise, between 5° C. and 10° C. The mixture was stirred for 1 hour, between 5° and 10° C. and the temperature was then allowed to rise. The solution obtained was taken up with 2 liters of water. Acetic acid was added until a pH of 4 was obtained and the chloroform was distilled off. The solution remaining was filtered and then made alkaline with 30% sodium hydroxide until a color change of phenolphthalein was observed. The oil formed was decanted and extracted with ether and the solution containing ether was then dried over potassium carbonate. The ether was distilled off, the distillation towards the end being carried out under vacuum, until a constant weight was obtained.

Workup

  1. temperaturewhile maintaining the temperature between 0° C. and 5° C
  2. stirringThe mixture was stirred for 1 hour, between 5° and 10° C.
  3. customThe solution obtained
  4. customwas obtained
  5. distillationthe chloroform was distilled off
  6. filtrationThe solution remaining was filtered
  7. customThe oil formed
  8. customwas decanted
  9. extractionextracted with ether
  10. additionthe solution containing ether
  11. dry with materialwas then dried over potassium carbonate
  12. distillationThe ether was distilled off
  13. distillationthe distillation towards the end
  14. customwas obtained

Sources & evidence

ORD record
ord-944dda837fef40208fbb15238cdb7147
Source dataset
uspto-grants-1991_04
Patent number
US05006570

Reaction notes

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